Thoma Bravo's Behind the Deal

In the final episode of Season 4, Orlando Bravo sits down with Dayforce Founder and CEO David Ossip for a deep dive into what it takes to scale a company without losing its edge. From transforming Ceridian into Dayforce to building a business that has surpassed $2 billion in revenue, David shares the leadership philosophy behind that growth—including a standout year with 43% sales expansion. At th...

In this episode of Behind the Deal, Thoma Bravo Founder and Managing Partner Orlando Bravo sits down with Partner Tara Gadgil and Dayforce Founder & CEO David Ossip to unpack one of the firm’s most significant investments—a $12.3 billion acquisition of Dayforce. They explore what set Dayforce apart in the human capital management space, from its single data architecture to its ability to replace u...

In this special re-release of Behind the Deal—now brought to life in video—Orlando Bravo sits down with Thoma Bravo co-founder Carl Thoma for a conversation on the origins of modern private equity. Widely regarded as one of the pioneers of the industry, Carl shares how he developed the “buy and build” strategy, why discipline around risk and valuation matters more than ever and how mentorship shap...

In this episode of Beyond the Deal, Thoma Bravo Partner Carl Press is joined by Adam Kinalski and Sam Yules to tell the inside story of building the Explore platform from the ground up. What started as a blank slate in 2019 has grown into a high-velocity investment platform focused on emerging enterprise software leaders. The team shares how Explore was created to stay true to Thoma Bravo’s middle...

In this episode of Behind the Deal, Thoma Bravo Partner Carl Press and Principal Adam Kinalski are joined by Exostar CEO Richard Addi to tell the story behind one of the firm’s most hard-fought investments. Exostar, a mission-critical platform serving the aerospace and defense industry, wasn’t for sale. What followed was a multi-year effort to build trust with six joint venture shareholders, navig...

At Thoma Bravo’s 2025 AI Summit, Partner Hudson Smith sits down with Olo Founder and CEO Noah Glass to unpack one of the firm’s most compelling recent investments. From its early days as a text-based ordering tool to becoming a category leader powering digital experiences for over 750 restaurant brands, Olo has spent two decades shaping how consumers interact with restaurants. In this conversation...

In this episode of Beyond the Deal, Thoma Bravo Senior Partner A.J. Rohde and Principal Peter Hernandez sit down with Nearmap CEO Andy Watt for a candid conversation about leadership, culture and building a global technology company from Australia. Andy shares the story of how a move from Scotland to Sydney turned into a decades-long journey with a leading Australian technology company. The group...

In this episode of Thoma Bravo’s Behind the Deal, Senior Partner A.J. Rohde and Principal Peter Hernandez sit down with Nearmap CEO Andy Watt to unpack Thoma Bravo’s investment in Nearmap and the company’s evolution from an aerial imagery provider into a global property intelligence platform. They discuss how the deal originated, what made Nearmap stand out, the complexities of taking an Australia...

This week on Thoma Bravo's Beyond the Deal, the spotlight turns inward. Managing Partner Holden Spaht and Partner Brian Jaffee share their origin stories at Thoma Bravo — what the firm looked like in its early days, how responsibility comes fast, and why mentorship and entrepreneurialism sit at the center of the culture. From cold outreach and the firm’s early focus on software to leading exits an...

In this episode of Thoma Bravo’s Behind the Deal, Managing Partner Holden Spaht and Partner Brian Jaffee revisit the take-private and sale of Ellie Mae — a leading U.S. mortgage loan origination system — and how a $3.7B investment became an $11B exit to Intercontinental Exchange (ICE) just over a year later. They break down the original investment thesis, the operational playbook, pricing and pack...

In this episode of Beyond the Deal, Intel 471 CEO and Co-Founder Jason Passwaters joins Thoma Bravo Partner Adam Solomon for a candid conversation about the experiences that shaped him as a leader. Passwaters reflects on his early years in the U.S. Marines — from infantry to counterintelligence — and the lessons he carried into building a global cybersecurity company. He shares how resourcefulness...

In this episode, Thoma Bravo Partner Adam Solomon and SVP Chandler Gay break down the firm’s investment in Intel 471, a bootstrapped, founder-led cyber threat intelligence company trusted by many of the world’s largest enterprises. They revisit the rigorous diligence process — including moments when the deal nearly fell apart — and explain what ultimately set the business apart: proprietary, highl...

In this episode of Thoma Bravo’s Behind the Deal, Managing Partner Holden Spaht sits down with Charles Gottdiener, CEO of Anaplan, and Leagh Turner, CEO of Coupa, to discuss how enterprise software leaders are turning AI innovation into real business impact. Drawing on their experience as both builders and users of AI, they share how AI is driving productivity, reshaping operating models, and expa...

Recorded live at Thoma Bravo’s 2025 AI Summit, this episode features a fireside chat between Thoma Bravo Founder and Managing Partner Orlando Bravo and IBM CEO Arvind Krishna. Krishna shares an operator’s view on why AI is unequivocally good for software—boosting developer productivity, expanding entry-level hiring, and unlocking billions in back-office automation that IBM has reinvested into soft...

What separates good CEOs from great ones? According to Proofpoint CEO Sumit Dhawan, it’s the ability to build belief. In this episode of Beyond the Deal, Thoma Bravo Managing Partner Seth Boro sits down with Sumit to discuss the leadership principles behind scaling a high-performing, human-centric cybersecurity company. From growing up in Delhi and learning the value of hard work and ownership, to...

Season 4 of Behind the Deal kicks off with a deep dive into Proofpoint, a key investment within Thoma Bravo’s cybersecurity portfolio. Seth Boro and Andrew Almeida reflect on the conviction behind the firm’s largest software buyout at the time, while Proofpoint CEO Sumit Dhawan shares how the company has scaled, evolved its platform, and stayed ahead of rapidly growing cyber threats in an AI-drive...

Thoma Bravo returns with Season 4 of Behind the Deal—the chart-topping, award-winning podcast that goes inside the strategy, leadership, and conviction behind the world’s largest software-focused investment firm. This season brings listeners to the forefront of the software and AI landscape. Hear from Proofpoint’s CEO on how AI is reshaping cybersecurity and what it takes to lead at scale in an in...

In this bonus episode, Thoma Bravo founder and managing partner, Orlando Bravo joins View From The Top from Stanford GSB for a candid conversation on his nonlinear journey—from leaving a small town in Puerto Rico to building one of the world’s leading software investment firms. Orlando opens up about early career setbacks—including rejection, failed deals, and the mentors who shaped his investing...

Inspired by the book Getting Real, HubSync Founder and CEO John McGowan explains to Thoma Bravo Partner Ross Devor how operating under tight timelines and budgets with a lean team forced HubSync to focus on an engineer-first approach, providing a foundation for a company that was able to scale.

HubSync started as a bootstrapped idea from John McGowan, a former Big Four tax professional who saw the tech gap in mid-sized CPA firms. In this episode of ‘Behind the Deal,’ Thoma Bravo Partner Ross Devor talks with John about how he turned early consulting work into a profitable SaaS business, the strategy behind landing over 40% of the top 25 accounting firms, and how product market fit shaped...

In the Beyond the Deal mini-sode with Thoma Bravo’s A.J. Rohde and Peter Hernandez, hear NextGen Healthcare CEO David Sides explain his approach to leadership, inspired by his family’s medical roots, and how NextGen Healthcare grew into one of the most trustworthy companies in America. For more information on Thoma Bravo's Behind the Deal, visit https://www.thomabravo.com/behindthedealLearn more a...

In this episode, Thoma Bravo Senior Partner A.J. Rohde sits down with Peter Hernandez, a Senior Vice President on our Discover team, to detail the strategic take-private of NextGen Healthcare, a leading provider of innovative, cloud-based healthcare technology solutions. They are joined in the studio by NextGen Healthcare CEO David Sides and discuss their bold vision for the future of healthcare I...

In this Beyond the Deal minisode, hear Instructure CEO Steve Daly share how his past experiences informed his mission to create a results-oriented, customer-centric company and a culture where people genuinely enjoy coming to work. Thoma Bravo Managing Partner, Holden Spaht, and Partner, Brian Jaffee, speak with Steve Daly about his leadership philosophy and building a company culture that emphasi...

Instructure’s Canvas, the learning management system used by over 4,000 school districts and 2,500 higher education institutions, became a lifeline during the pandemic. On this episode of Behind the Deal, Thoma Bravo Managing Partner Holden Spaht and Partner Brian Jaffee sit down with Instructure CEO Steve Daly to discuss how they worked together to refocus Instructure to grow into a leading EdTec...

Ping Identity Founder & CEO, Andre Durand, explains that in a 10-10 culture, “the how matters as much as the what.” Over time, through his experience as a multi-time founder, he has come to resonate with one simple cultural north star that he refers to as “10-10” to strike a balance between performance and attitude. In this Beyond the Deal minisode, Andre Durand sits down with Thoma Bravo’s Orland...